A Cooperative Ternary Catalysis System for Asymmetric Lactonizations of α-Ketoesters

被引：12
|
作者：
Murauski, Kathleen J. R. [1 ]
Walden, Daniel M. [2 ]
Cheong, Paul Ha-Yeon [2 ]
Scheidt, Karl A. [1 ]
机构：
[1] Northwestern Univ, Dept Chem, Ctr Mol Innovat & Drug Discovery, 2145 Sheridan Rd, Evanston, IL 60208 USA
[2] Oregon State Univ, Dept Chem, 153 Gilbert Hall, Corvallis, OR USA
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 21期
关键词：
N-heterocyclic carbene; NHC; ternary catalysis; lactone; cooperative catalysis; Umpolung; homoenolate; N-HETEROCYCLIC CARBENE; HYDROGEN-BOND DONORS; CONJUGATE UMPOLUNG; GAMMA-BUTYROLACTONES; BRONSTED ACID; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CARBON ACTIVATION; TERTIARY-AMINES; DUAL CATALYSIS;
D O I：
10.1002/adsc.201701015
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A general and enantioselective N-heterocyclic carbene (NHC)-catalyzed lactonization of simple enals and alpha-ketoesters has been discovered using a new ternary cooperative catalytic system. The highly selective annulation was achieved by using a combination of a chiral NHC, a hydrogen-bond donor, and a metal salt, facilitating self-assembly of the reactive partners. A proposed model for this new mode of NHC chiral relay catalysis is supported by experimental and computational mechanistic studies.
引用
收藏
页码：3713 / 3719
页数：7
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